When was the last time you went to a magic lantern show? Or a melodrama? And liked it? Some forms of entertainment don’t hold up over time. Imagine a curly-mustached Victorian fop trying to convince you that no, seriously pantomimes are riveting. That’s how it feels explaining Oregon Trail to people who were too young to live it firsthand. But now that Oregon Trail is available to play online, there are going to be a lot of folks in the 23-and-under* crowd trying to understand the fuss – so I’ll make an effort.
The Life And Times Of ’80s and ’90s Kids

I call this costume ‘Annie Hall Of Green Gables.’
I’ve mentioned this before, but there was this weird trend in the early-mid 90s that nobody ever talks about. It’s not leggings or crop tops, which if anything are over-represented in 90s nostalgia. No, it was this thing where it was sort of normal for a child to be into the 1800s. A new version of Little Women came out, those American Girl books were everywhere, and moms watched Dr. Quinn. The Indian In The Cupboard was surprisingly popular. Craft books taught you how to make yarn dolls like Laura Ingalls. We were standing on the cusp of the digital age, playing with doll-sized butter churns.
In addition to old-timey pursuits like microwaving popcorn right on the cob just like they did in Colonial Williamsburg, us early millennials were the first generation to use computers as soon as we started school. Well, they were less like computers and more like giant graphing calculators. The screens were all-black with green or orange lettering and simple line graphics. A big part of every computer class was booting up your computer – not because it was exciting, but because it took ten minutes. Those of us who were lucky had Nintendo at home, and later, maybe a Sega system. Still, computer games were new and exciting and required “floppy disks.” There weren’t many choices, but kids and lazy substitute teachers alike loved Oregon Trail. Adults appreciated that it was educational – in that it provided a one-sided view of Manifest Destiny, I suppose. And kids loved it, because it represented a world …
Where Children Were Gods
I once read that youngest children are drawn to animals because they enjoy having someone that they could be the boss of. As a youngest child, I’d argue that we just liked being around living things that couldn’t pick on us, but I digress. Sometimes a kid does like being in charge of things. Every game of Oregon Trail was a tiny, horrifying example of what would happen if kids ruled the world – like a virtual Lord Of The Flies.
You would think that the goal of any game would be to win it. That discounts just how cruel and terrible children can be. Sometimes, you’d play just to see how disastrous you could make the lives of the characters. Here’s how:
- You were allowed to name the wagon party. That meant that the most common names in Oregon Trail character history were probably Poop, Butt, Jesus and (Sibling’s Name) Sucks.
- You’d become a dreadful taskmaster, especially if the game handed you a low-income profession. The harshest sentence? Grueling pace and meager rations. That’s also the title of my future memoirs. And with that burden, it’s no wonder that…
- Bitches got dysentery. And bitches who get dysentery get buried under a solitary rock along the roadside before we continue on our journey. Sorry, Butt.
- “I tried to ford the river and my f***ing oxen died.” That was one of the biggest Facebook groups of the 2004-2006 era, and a universal experience during Oregon Trail’s heyday. When you got to the river you could hire a local to ferry it across, caulk the wagon, or sort of just hurl yourself headlong into the river. That’s how I remember it anyway. And I always found myself thinking, shouldn’t we have figured this out before we got to the damn river?
- We killed the American Buffalo. When you’d go hunting, those slow-ass buffalo mosied across the screen, leaving you ample time to shoot them. You’d kill every buffalo that ambled by. Then, you’d be informed that you could only bring 100 pounds of meat into your wagon and had to leave all that buffalo carrion to fester in the prairie sun. We knew that would happen. We just wanted to hear the hollow thud when they died. Children are sick. Someone, please make a horror movie in which all of the events of the Westward Expansion – including the near-extinction of the buffalo – were under the control of 7-year-old Kimberly in Miss Smith’s computer class in 1992.
Ain’t No Party Like An Oregon Trail Party Cuz An Oregon Trail Party Proffers a Tombstone Generator When You Die From Pooping Too Much
On one hand, children were pioneer overlords in Oregon Trail – but on the other, the cruel hand of fate was always at play. It was like the game of Life, but instead of teaching children that you may fritter your life away in middle-management at a bank, it taught you that sometimes you do your best and thieves still steal all of your oxen in your sleep. Even if you played the game the “right way,” giving your settlers proper Oregon Trail names like Rebecca and Amos and setting a pace that would get you to Oregon before winter without killing you from exhaustion (before it was the trendiest cause of celebrity hospitalization), there were no guarantees that you’d arrive in the promised land. The dream of the 1850’s was alive in Portland – but would you be alive to see it? Here are some ways you could die:
- Measles
- Snakebite
- Broken limbs
- Drowning
- Cholera
- Exhaustion
- Typhoid
- Failing to save your progress at the end of a class period.
Godspeed, 90s kids. You have a 40-minute computer class ahead of you, and your teacher has laryngitis. During that time you may reach the promised land, and you may die from drinking river water. And even if you live, PoopfaceJesus may not. Oh, cruel world.
*This probably varies depending on how outdated your school’s computer game library was.While later versions of Oregon Trail came out on CD-ROM, I think that after the early-mid 90s, there were more games to chose from and Oregon Trail was no longer the only, um, ox on the prairie? So to speak.
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